Ethanol → HCID 20271288, compound

Crude sodium 2-(4-picolylthio)propionate (approximately 7 g.) was taken up in 100 ml. of absolute ethanol and approximately 5 cc. of 3A molecular sieves were added. Dry hydrogen chloride was bubbled into the reaction mixture, which was refluxed for 75 minutes, while continuing to saturate with hydrogen chloride during the initial 15 minutes. The mixture was cooled to room temperature and allowed to stir overnight (approximately 16 hours). The mixture was filtered through diatomaceous earth and concentrated to a semi-solid mixture. The esterification step was repeated on this mixture, except saturation with hydrogen chloride was continued during 1 hour of reflux and refluxing was continued overnight. The reaction mixture was cooled to room temperature, filtered through diatomaceous earth and evaporated to an oil. The oil was extracted with chloroform, leaving filterable salts behind, and the chloroform stripped to yield ethyl 2-(4-picolylthio)- propionate (waxy solid; ir (KBr) 3.0, 3.5, 5.75, 6.15, 6.30, 6.70, 8.6, 12.25,μ; m.s.: m/e calcd: 225; found: 225, 152, 124, 102, 92, 45).

1. customDry hydrogen chloride was bubbled into the reaction mixture, which
2. temperaturewas refluxed for 75 minutes
3. concentrationto saturate with hydrogen chloride during the initial 15 minutes
4. filtrationThe mixture was filtered through diatomaceous earth
5. concentrationconcentrated to a semi-solid mixture
6. waitwas continued during 1 hour
7. temperatureof reflux
8. temperaturerefluxing
9. waitwas continued overnight
10. temperatureThe reaction mixture was cooled to room temperature
11. filtrationfiltered through diatomaceous earth
12. customevaporated to an oil
13. extractionThe oil was extracted with chloroform
14. customleaving filterable salts behind, and the chloroform

ORD record

ord-5d16b903beee4ecbb21c7f0afffb1c89

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04535084